Literature DB >> 23407887

Catalytic X-H insertion reactions based on carbenoids.

Dennis Gillingham1, Na Fei.   

Abstract

Catalysed X-H insertion reactions into diazo compounds (where X is any heteroatom) are a powerful yet underutilized class of transformations. The following review will explore the historical development of X-H insertion and give an up-to-date account of the metal catalysts most often employed, including an assessment of their strengths and weaknesses. Despite decades of development, recent work on enantioselective variants, as well as applying catalytic X-H insertion towards problems in chemical biology indicate that this field has ample room for innovation.

Entities:  

Year:  2013        PMID: 23407887     DOI: 10.1039/c3cs35496b

Source DB:  PubMed          Journal:  Chem Soc Rev        ISSN: 0306-0012            Impact factor:   54.564


  42 in total

Review 1.  Diazo Compounds: Versatile Tools for Chemical Biology.

Authors:  Kalie A Mix; Matthew R Aronoff; Ronald T Raines
Journal:  ACS Chem Biol       Date:  2016-10-26       Impact factor: 5.100

2.  Selective Functionalization of Aliphatic Amines via Myoglobin-catalyzed Carbene N-H Insertion.

Authors:  Viktoria Steck; Gopeekrishnan Sreenilayam; Rudi Fasan
Journal:  Synlett       Date:  2019-07-11       Impact factor: 2.454

3.  Rhodium-catalyzed NH insertion of pyridyl carbenes derived from pyridotriazoles: a general and efficient approach to 2-picolylamines and imidazo[1,5-a]pyridines.

Authors:  Yi Shi; Anton V Gulevich; Vladimir Gevorgyan
Journal:  Angew Chem Int Ed Engl       Date:  2014-10-21       Impact factor: 15.336

4.  Activity-Directed Synthesis of Inhibitors of the p53/hDM2 Protein-Protein Interaction.

Authors:  Adam I Green; Fruzsina Hobor; Christopher P Tinworth; Stuart Warriner; Andrew J Wilson; Adam Nelson
Journal:  Chemistry       Date:  2020-08-04       Impact factor: 5.236

Review 5.  Applications of Nonenzymatic Catalysts to the Alteration of Natural Products.

Authors:  Christopher R Shugrue; Scott J Miller
Journal:  Chem Rev       Date:  2017-06-05       Impact factor: 60.622

6.  Site-Selective and Stereoselective O-Alkylation of Glycosides by Rh(II)-Catalyzed Carbenoid Insertion.

Authors:  Jicheng Wu; Xiaolei Li; Xiaotian Qi; Xiyan Duan; Weston L Cracraft; Ilia A Guzei; Peng Liu; Weiping Tang
Journal:  J Am Chem Soc       Date:  2019-12-03       Impact factor: 15.419

Review 7.  Cycloaddition reactions of enoldiazo compounds.

Authors:  Qing-Qing Cheng; Yongming Deng; Marianne Lankelma; Michael P Doyle
Journal:  Chem Soc Rev       Date:  2017-08-29       Impact factor: 54.564

8.  Cytochrome P450-Catalyzed Insertion of Carbenoids into N-H Bonds.

Authors:  Z Jane Wang; Nicole E Peck; Hans Renata; Frances H Arnold
Journal:  Chem Sci       Date:  2014-02-01       Impact factor: 9.825

9.  Metal Substitution Modulates the Reactivity and Extends the Reaction Scope of Myoglobin Carbene Transfer Catalysts.

Authors:  Gopeekrishnan Sreenilayam; Eric J Moore; Viktoria Steck; Rudi Fasan
Journal:  Adv Synth Catal       Date:  2017-04-12       Impact factor: 5.837

10.  Rh(II)-Catalyzed Reactions of Diazoesters with Organozinc Reagents.

Authors:  Robert Panish; Ramajeyam Selvaraj; Joseph M Fox
Journal:  Org Lett       Date:  2015-08-04       Impact factor: 6.005

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